Composition for Silicone Rubber Masses

Abstract

A composition containing a curing agent for silicone rubber masses and an organosilane, in particular a heterocyclic organosilane, as well as sealing agents, adhesives or coating agents containing this composition, the use of this composition as a sealing agent, adhesive or coating agent and the use of an organosilane according to the invention, in particular a heterocyclic organosilane as a water scavenger, alcohol scavenger and/or hydroxide ion scavenger and, after activation, as an adhesion promoter in silicone rubber masses is presented and described.

1 . Composition comprising
 a. a curing agent for silicone rubber masses comprising a compound having the general structural formula R 1   m Si(R) 4-m ,
 wherein 
 each R 1  independently represents an optionally substituted straight-chain or branched C1 to C16 alkyl group, an optionally substituted straight-chain or branched C2 to C16 alkenyl group or an optionally substituted C4 to C14 aryl group, 
 m is an integer from 0 to 2, 
 each R is independently selected from the group consisting of
 a hydroxycarboxylic acid ester residue having the general structural formula (I): 
 
   
       
         
           
           
               
               
           
         
         
           
             wherein 
             each R 2  independently represents H or an optionally substituted, straight-chain or branched C1 to C16 alkyl group, an optionally substituted, straight-chain or branched C2 to C16 alkenyl group, or an optionally substituted, straight-chain or branched C2 to C16 alkynyl group, or a C4 to C14 aryl group, 
             each R 3  independently represents H or an optionally substituted, straight-chain or branched C1 to C16 alkyl group, an optionally substituted, straight-chain or branched C2 to C16 alkenyl group, or an optionally substituted, straight-chain or branched C2 to C16 alkynyl group, or a C4 to C14 aryl group, 
             R 4  represents an optionally substituted, straight-chain or branched C1 to C16 alkyl group, an optionally substituted, straight-chain or branched C2 to C16 alkenyl group or an optionally substituted, straight-chain or branched C2 to C16 alkynyl group, a C4 to C14 cycloalkyl group, a C5 to C15 aralkyl group or a C4 to C14 aryl group, 
             R 5  is C or an optionally substituted saturated or partially unsaturated cyclic ring system having 4 to 14 C atoms or an optionally substituted aromatic group having 4 to 14 C atoms, and 
             n is an integer from 0 to 10,
 a hydroxycarboxylic acid amide residue of the general structural formula (II): 
 
           
         
       
       
         
           
           
               
               
           
         
         
           
             wherein 
             each R 6  independently represents H or an optionally substituted, straight-chain or branched C1 to C16 alkyl group, an optionally substituted, straight-chain or branched C2 to C16 alkenyl group, or an optionally substituted, straight-chain or branched C2 to C16 alkynyl group, or a C4 to C14 aryl group, 
             each R 7  or R 8  independently represents H or an optionally substituted, straight-chain or branched C1 to C16 alkyl group, an optionally substituted, straight-chain or branched C2 to C16 alkenyl group or an optionally substituted, straight-chain or branched C2 to C16 alkynyl group or a C4 to C14 aryl group,
 —O—C(O)—R 9 , wherein R 9  means H, an optionally substituted, straight-chain or branched C1 to C16 alkyl group, an optionally substituted, straight-chain or branched C2 to C16 alkenyl group or an optionally substituted, straight-chain or branched C2 to C16 alkynyl group, a C4 to C14 cycloalkyl group or a C4 to C14 aryl group, and 
 —O—N═CR 10 R 11 , wherein R 10  and R 11  independently mean H, an optionally substituted straight-chain or branched C1 to C16 alkyl group, an optionally substituted straight-chain or branched C2 to C16 alkenyl group or an optionally substituted straight-chain or branched C2 to C16 alkynyl group, a C4 to C14 cycloalkyl group or a C4 to C14 aryl group, 
 
             and 
           
         
         b. at least one organosilane as water scavenger, alcohol scavenger and/or hydroxide ion scavenger and 
         c. optionally at least one organopolysiloxane. 
       
     
     
         2 . Composition according to  claim 1  characterized in that a heterocyclic organosilane is contained, wherein at least one silicon atom and at least one heteroatom are directly linked to one another and the heteroatom is selected from the group consisting of N, P, S or O. 
     
     
         3 . Composition according to  claim 2  characterized in that one or more heterocyclic organosilanes are selected from the group of the general structural formulae (III), (IIIa), (IV), (IVa), (V), (Va) or mixtures thereof: 
       
         
           
           
               
               
           
         
         wherein
 a is 0, 1 or 2; 
 x means 0 to 100; 
 y means 1 to 1000; 
 n means 0 to 6
 each R a , R b , R c , R d , R e , R f  or R g  is independently H or an optionally substituted, straight-chain or branched C1 to C20 alkyl group, an optionally substituted, straight-chain or branched C2 to C20 alkenyl group, an optionally substituted C3 to C20 cycloalkyl group, an optionally substituted C4 to C20 cycloalkenyl group, an optionally substituted, straight, branched or cyclic C4 to C20 alkynyl group or an optionally substituted, straight or branched C2 to C20 heteroalkyl group, an optionally substituted, straight, branched or cyclic C3 to C20 heteroalkenyl group or an optionally substituted C4 to C14 aryl or heteroaryl group; 
 each R A  and/or R B  and/or (R C ) n  taken together form a 4- to 10-membered ring. 
 
 
       
     
     
         4 . Composition according to  claim 1 , characterized in that one or more organosilanes are selected from the group consisting of iminosilanes of the general structural formula (VII), silanoaminosilanes of the general structural formula (VIII), non-cyclic organosilanes of the general structural formula (IX), amino-protecting group-containing organosilanes (IXa) to (IXe) derived from the general structural formula (IX) or mixtures thereof: 
       
         
           
           
               
               
           
         
         wherein
 R h  is C or Si; 
 each R i , R j  independently mean H, —C(O)R t , an optionally substituted straight-chain or branched C1 to C16 alkyl group, an optionally substituted straight-chain or branched C2 to C16 alkenyl group, or an optionally substituted C4 to C14 aryl group 
 each R k , R l , R m  independently mean H, —C(O)R t , an optionally substituted, straight-chain or branched C1 to C16 alkyl group, an optionally substituted, straight-chain or branched C2 to C16 alkenyl group, or an optionally substituted C4 to C14 aryl group 
 each R n , R o , R p , R q , R r , R s  independently mean H, —O—R t , —C(O)—R t , —COOR t , an optionally substituted, straight-chain or branched C1 to C16 alkyl group, an optionally substituted, straight-chain or branched C2 to C16 alkenyl group, or an optionally substituted C4 to C14 aryl group 
 each R t , R u  independently mean H, —OR i , —C(O)R i , —C(O)CF 3 , —COOR i , an optionally substituted straight-chain or branched C1 to C16 alkyl group, an optionally substituted straight-chain or branched C2 to C16 alkenyl group, an optionally substituted C4 to C14 aryl group, or a protecting group in particular a tert-butoxycarbonyl group, a fluorenylmethoxycarbonyl group, a benzyloxycarbonyl group, an allyloxycarbonyl group, an optionally substituted isoindole-1,3-dione group or a 3-methyl-benzenesulfone group, and 
 z is an integer from 1 to 30. 
 
       
     
     
         5 . Composition at least comprising a mixture obtainable by mixing at least one curing agent according to claim  1 a with at least one organosilane 4b and/or a heterocyclic organosilane according to claim  3 b. 
     
     
         6 . Composition according to  claim 1 , characterized in that the organosilane is contained at a maximum of 3 wt.-% based on the total weight of the composition. 
     
     
         7 . Composition according to  claim 2 , characterized in that the heterocyclic organosilane is a 4- to 10-membered heterocycle. 
     
     
         8 . Composition according to  claim 2  characterized in that the heterocyclic organosilane is a 5- to 6-membered heterocycle. 
     
     
         9 . Composition according to  claim 6 , characterized in that the heterocycle contains at least one N. 
     
     
         10 . Composition according to  claim 1 , characterized in that the silicon atom carries at least one OR d  residue and each R d  independently carries H or an optionally substituted, straight-chain or branched C1 to C20 alkyl group, an optionally substituted, straight-chain or branched C2 to C20 alkenyl group, an optionally substituted C3 to C20 cycloalkyl group, represents an optionally substituted C4 to C20 cycloalkenyl group, an optionally substituted, straight, branched or cyclic C4 to C20 alkynyl group or an optionally substituted, straight or branched C2 to C20 heteroalkyl group, an optionally substituted, straight, branched or cyclic C3 to C20 heteroalkenyl group or an optionally substituted C4 to C14 aryl or heteroaryl group. 
     
     
         11 . Composition according to  claim 2 , characterized in that the heterocyclic organosilane has at least one of the following structural formulae: 
       
         
           
           
               
               
           
         
         wherein
 a is 0, 1 or 2; 
 x means 0 to 100; 
 y means 1 to 1000; 
 n means 0 to 6
 each R a , R b , R c , R d , or R g  is independently H or an optionally substituted, straight-chain or branched C1 to C20 alkyl group, an optionally substituted, straight-chain or branched C2 to C20 alkenyl group, an optionally substituted C3 to C20 cycloalkyl group, an optionally substituted C4 to C20 cycloalkenyl group, an optionally substituted, straight, branched or cyclic C4 to C20 alkynyl group or an optionally substituted, straight or branched C2 to C20 heteroalkyl group, an optionally substituted, straight, branched or cyclic C3 to C20 heteroalkenyl group or an optionally substituted C4 to C14 aryl or heteroaryl group; 
 R A  and/or R B  and/or (R C ) n  taken together form a 4- to 10-membered ring. 
 
 
       
     
     
         12 . Composition comprising,
 a. a curing agent for silicone rubber masses comprising a compound having the general structural formula R 1   m Si(R) 4-m ,
 wherein 
 each R 1  independently means an optionally substituted straight-chain or branched C1 to C16 alkyl group, an optionally substituted straight-chain or branched C2 to C16 alkenyl group or an optionally substituted C4 to C14 aryl group, 
 m is an integer from 0 to 2, 
 each R is independently selected from the group consisting of
 —O—N═CR 10 R 11 , wherein R 10  and R 11  independently means H, an optionally substituted straight-chain or branched C1 to C16 alkyl group, an optionally substituted straight-chain or branched C2 to C16 alkenyl group or an optionally substituted straight-chain or branched C2 to C16 alkynyl group, a C4 to C14 cycloalkyl group or a C4 to C14 aryl group, 
 and 
 
   b. at least one heterocyclic organosilane having at least one of the following structural formulae:   
       
         
           
           
               
               
           
         
         wherein
 a is 0, 1 or 2; 
 x means 0 to 100; 
 y means 1 to 1000; 
 n means 0 to 6;
 each R a , R b , R c , R d  or R g  is independently H or an optionally substituted, straight-chain or branched C1 to C20 alkyl group, an optionally substituted, straight-chain or branched C2 to C20 alkenyl group, an optionally substituted C3 to C20 cycloalkyl group, an optionally substituted C4 to C20 cycloalkenyl group, an optionally substituted, straight, branched or cyclic C4 to C20 alkynyl group or an optionally substituted, straight or branched C2 to C20 heteroalkyl group, an optionally substituted, straight, branched or cyclic C3 to C20 heteroalkenyl group or an optionally substituted C4 to C14 aryl or heteroaryl group; 
 each R A  and/or R B  and/or (R C ) n  taken together form a 4- to 10-membered ring. 
 
 
       
     
     
         13 . Composition according to  claim 12 , characterized in that it contains at least one organopolysiloxane. 
     
     
         14 . Composition according to  claim 12 , characterized in that it contains
 a) 30 to 70 wt.-% α, ω-dihydroxydialkyl organopolysiloxane,   b) 1 to 10 wt.-% of curing agent and   c) 0.1 to 10 wt.-% organosilane.   
     
     
         15 . A process for preparing a composition comprising the following steps:
 (i) Mixing an organopolysiloxane with a crosslinker or a crosslinker mixture according to  claim 1  under vacuum;   (ii) Mixing in an organosilane and a catalyst under vacuum, wherein the catalyst is selected from the group consisting of tin carboxylates, titanium, zirconium or aluminium compounds.   
     
     
         16 . Use of an organosilane of  claim 1  as a water scavenger, alcohol scavenger and/or hydroxide ion scavenger. 
     
     
         17 . Use of a composition of  claim 1  for the manufacture of a silicone rubber composition. 
     
     
         18 . Use of a reaction product of at least one organosilane with water, as adhesion promoter. 
     
     
         19 . Use of a composition of  claim 1  as a sealant, adhesive, potting compound or coating agent. 
     
     
         20 . Use of an organosilane  claim 1  as a stabilizer, characterized in that it carries a trialkylsilyl group on at least one heteroatom.